(1S,9aR,11aS)-9a,11a-Dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid (1,1,3,3-tetramethyl-butyl)-amide

ID: ALA24729

Max Phase: Preclinical

Molecular Formula: C27H44N2O2

Molecular Weight: 428.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)CC(C)(C)NC(=O)[C@H]1CCC2C3CNC4=CC(=O)CC[C@]4(C)C3CC[C@@]21C

Standard InChI:  InChI=1S/C27H44N2O2/c1-24(2,3)16-25(4,5)29-23(31)21-9-8-19-18-15-28-22-14-17(30)10-12-27(22,7)20(18)11-13-26(19,21)6/h14,18-21,28H,8-13,15-16H2,1-7H3,(H,29,31)/t18?,19?,20?,21-,26+,27-/m1/s1

Standard InChI Key:  YMQRRHUFVPWJAP-CKBGLNIBSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  1  0  0  0  0  0999 V2000
    4.0375   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -6.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5 14  1  0
  6  4  1  0
  8  7  1  1
  8  1  1  0
  9 13  1  0
 10  3  2  0
 11  7  1  0
 12  1  1  0
 13  6  1  0
 14 12  1  0
 15  4  1  0
 16  2  1  0
 17  8  1  0
 18 11  1  0
 19 24  1  0
 20  7  2  0
 21 19  2  0
 22 18  1  0
 23 22  1  0
 24 16  1  0
  1 25  1  1
  2 26  1  1
 27 18  1  0
 28 18  1  0
 29 23  1  0
 30 23  1  0
 31 23  1  0
 15 17  1  0
  6  5  1  0
  3  9  1  0
 10 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA24729

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 428.66

Molecular Weight (Monoisotopic): 428.3403

AlogP: 5.23

#Rotatable Bonds: 3

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.40

CX LogP: 4.35

CX LogD: 4.35

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: 0.92

References

1. Kenny B, Ballard S, Blagg J, Fox D..  (1997)  Pharmacological options in the treatment of benign prostatic hyperplasia.,  40  (9): [PMID:9135028] [10.1021/jm960697s]

Source

Source(1):

• Scientific Literature